The olefin metathesis reaction, also known as the olefin disproportionation reaction, has been used for some time in the petroleum industry to metathesize propane into polymerization grade ethene and high quality butenes. Metatheses of 1-octene to ethene and 7-tetradecene have been performed. Bailey, Catalysis Reviews 3:37 (1970). The catalysts necessary for the reaction are generally known, see, e.g. Bailey, above; Mol. et al., Advances in Catalysis, 24, 131 (1975); Calderon, Acts. of Chem. Res., 5, 127 (1972); Calderon, et al., Angew. Chem. Int. Ed., 15 401 (1976). Mol, et al. also describe the use of the metathesis reaction to form macrocyclic compounds and the production of detergent range linear alkenes from lower alkenes. These workers have typically confined their synthetic efforts to the production of alkenes.
The literature has recently described hydrometallation reactions, specifically hydrozirconation reactions, using bis-cyclopentadienyl zirconium hydrochloride (often abbreviated Cp.sub.2 ZrHCl). This compound adds across internal double bonds of an olefin and then migrates completely and rapidly to the end of the carbon chain. The terminal zirconium moiety can then be replaced by electrophilic groups under mild conditions. Hart, et al., JACS 96:8115 (1974); Bertelo, et al., JACS 97:228 (1975); Hart, et al., JACS 97:679 ;l (1975); Lahenger, et al., JACS 97:3851 (1975); Blackburn, et al., Tet. Ltr 3041 (1975). The hydrozirconation reaction is a convenient replacement for more traditional reactions, such as hydroboration, for converting olefins into terminal functional alkanes. See, e.g., Brown, et al., JACS 81:6434 (1959) and Logan, J. Org. Chem. 26:3657 (1961).
None of the workers in the art appear to have appreciated the convenience and ease of preparation of terminal functional alkanes using the present process, especially as it relates to the long-chain alkanes.